DE2857293A1 - PRE-PRODUCT OF A MEAT FLAVOR - Google Patents

Description

Our no. 22 568 D / v / l

The Procter & Gamble

Company

Cincinnati, Ohio, V.St.A.

Preliminary product of a meat flavor

The present invention relates to a preliminary product for a meat-like flavor and a method for producing meaty aroma or taste.

Great Porsche and development efforts were made made in the search for substances that give foods such as meat substitutes an authentic meat-like flavor can issue. Often the results of such attempts were disappointing, either because the flavor mixture was too high expensive or the resulting taste was not authentic.

The amino acid cysteine has been widely used in processes to produce "meaty" tastes. So became for example, cysteine reacted with fractionated wood smoke (US Pat. No. 2,918,576); with a furan compound (US-PS 2,934,435); with glyceraldehyde (U.S. Patent 2,934,436); and with a pentose or hexose monosaccharide (US Pat. No. 2,934,437) Cysteine is also found in more complicated, made-up reactions

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resulting flavors, which are described in US-PSS 3 365 306, 3,615,698, 3,615,600, 3,493,395 and 3,532,514

US Pat. No. 3,394,015 (International Flavors & Fragrances, Inc.) teaches a method of producing a "meaty" taste and aroma by converting a proteinaceous one Substance and a sulfur-containing compound, for example cysteine, in the absence of a monosaccharide.

S-Methy! -Methionine is also known as a substance that Adds flavor to foods. According to US-PS 3 9 ^ 0 500, a consumable material is given, for example Seafood, a shellfish flavor by adding a compound containing a dimethylthio group such as zum Example of an S-methyl methionine salt.

However, free dimethyl sulfide and hydrogen sulfide are unstable as food additives. Literally hundreds of other additives are described for improving the taste and / or aroma of meat substitutes and others Foods, some with either dimethyl sulfide or hydrogen sulfide, or a precursor of the one or other connections are to be used in combination.

However, it remained for the present invention to determine that the special combination of cysteine contains protein An authentic beef-style material and S-methyl-methionine Aroma develops that under the cooking conditions in the household the aroma of the individual components alone superior and surprisingly to a natural beef flavor produced under the same conditions is similar. One aim of the present invention is

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hence the provision of a flavor precursor that is used for Creation of beef-like taste can be used. Another object of the invention is to provide a Process for producing beef flavor in food under normal household cooking conditions can. Another object of the invention is to provide a surprisingly authentic beef taste from practical and cheap raw materials.

Another object of the invention is to provide a persistent flavor precursor in a food, that creates the meat-like taste when cooked.

Summary of the invention

The present invention relates to a preliminary product of a meat flavor which produces a meat-like taste, labeled by

A. a hydrogen sulfide precursor, consisting of cysteine, edible salts of cysteine, glutathione, edible salts of glutathione, edible proteinaceous sulfhydryl or cystine, preferably Cysteine,

Legs. Diethyl sulfide precursor, consisting of edible Salts or derivatives of S-methyl-methionine, S-methyl-4-methylthiobutyric acid, S-methyl-methylcysteine, S-methyl-j5-methylthiopropionic acid or S-methyl-methylthioacetic acid, preferably S-methylmethionine, and

C. an edible proteinaceous material, preferably Soy protein,

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being hydrogen sulfide precursor, dimethyl sulfide precursor and proteinaceous material are present in amounts that are effective are effective for producing a meat-like taste and aroma when the intermediate product is heated in the presence of a Amount of water.

When cooked, the pre-product creates an aroma that is surprisingly similar to cooked beef. It is intended that To be used in conjunction with other foodstuffs and flavorings that are also meat-like Create taste and / or change or enhance the aroma of the preliminary product during cooking. One of the advantages of the inventive flavor precursor is that the meat-like flavor is below the normal in the household Cooking conditions is created.

Description of preferred embodiments

An intermediate product suitable for producing a meat-like flavor preferably contains

A. a hydrogen sulfide precursor, for example from Cysteine, edible salts of cysteine or edible thiazolidine,

B. a dirnethyl sulfide precursor, for example from

S-methyl methionine or edible derivatives of

or
S-methyl-methionine, encapsulated in hard stock

Dimethyl sulfide and

C. an edible proteinaceous material, according to

heating this Vorpdoukts in the presence of water the meat-like aroma is created synergistically. The intermediate product can be added to foodstuffs, for example ground beef, or it can be used as food itself be used.

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* r

It is most preferred if the hydrogen sulfide precursor consists of cysteine and the dimethyl sulfide precursor consists of S-methyl-methionine. The amounts of hydrogen sulfide and dimethyl sulfide precursor materials used in the precursors of the present invention not critical, but should be sufficient to consume when heated in water in the presence of an edible proteinaceous Materials to produce a beef-like aroma. The amounts of these precursors depend, of course, on the type of material. Generally an amount of cysteine is from about 100 to about 50,000 parts per unit Million (ppm) per part of proteinaceous material (on a dry weight basis) and an amount of S-methyl-methinine of about 0.25 ppm to about 700 ppm is suitable for providing a beef-like flavor. Preferred cysteine and S-methyl methionine amounts are 1,000 to 50,000 ppm and 50 to 200 ppm, respectively, and most preferred are 2,000 up to 15,000 ppm cysteine and 25 to 175 ppm S-methyl methionine per part of proteinaceous material on a dry weight basis.

Of course, the dimethyl sulfide precursor according to the invention must be consumable. As dimethyl sulfide precursors In the present description, substances that produce dirnethyl sulfide by physical or chemical means apply. from Hard stock, for example fatty acid material with a melting point of about 60 C, encapsulated dimethyl sulfide is one acceptable dimethyl sulfide precursor. The derivatives of S-methyl-methionine and S-methyl-methylcysteine include the N-alkylamides, N-alkylamines and alkyl esters and alkylamides of that. Among derivatives of S-methyl-4-methylthiobutyric acid, S-methyl- "thiopropionic acid and S-methyl-thioacetic acid v / earth understood the alkyl or aryl esters or amides. Suitable salts are the chloride, bromide and iodide, and S-methyl methionine chloride is the most preferred salt.

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The cysteine component according to the invention must be consumable and can be present as a salt or in the form of the free base. Di-cysteine, L-cysteine, DL-cysteine, cysteine hydrochloride, etc. other edible salts of cysteine can be used. It is also intended to use cysteine precursors, especially edible, substituted thiazolidines. Edible substituted thiazolidines in the form of thiazolidines re-

reducing sugar, aldehyde thiazolidines and ketone thiazolidines are persistent cysteine precursors and are preferred. Edible protein-containing sulfhydryls include protein and other proteins that contain sulfhydryl groups.

The protein-containing materials which are suitable for use in the flavor precursor according to the invention include edible proteins, such as those obtained from vegetable protein sources, for example soybeans, sunflower seeds, Safflower seeds, corn, peanuts, wheat, peas, cottonseed, coconut, rapeseed, sesame seeds, leaf proteins and unicellular proteins like yeast. Since meat substitutes are generally made from proteinaceous material, the protein of the meat substitute itself can serve as the protein-containing substance required according to the invention. Even animal proteins can be used. These include milk, eggs, poultry, meat and fish. It was found, that the protein is heat coagulable or not heat coagulable and may be in denatured or undenatured form.

The method for producing a meat-like aroma according to the invention consists in that the preliminary product mixture heated in an aqueous medium to a temperature of 60 to 14O C until the meat-like aroma is created.

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Λ *

Without wishing to be bound by any theory, it is assumed that the flavor precursor according to the invention the improved meat-like flavor is produced at least in part by being cooked or heated in Presence of water, dimethyl sulfide (DMS) and hydrogen sulfide generated. The generation of these compounds in the space above the heated precursor mixture leads to a surprisingly authentic meaty aroma that is superior to the aroma obtained with either a Dimethyl sulfide precursor or a hydrogen sulfide precursor alone is produced. The proteinaceous material appears to have a catalytic effect on meat flavor development.

Some advantages of the flavor precursor are that it is more shelf-stable than foods impregnated with hydrogen sulfide or DMS, and that when cooked it creates a meat-like flavor that is synergistically superior to any component under household cooking conditions. Under cooking conditions in the household is meant temperatures between 60 and l80 ⁰ C, and typically from 80 to 100 ⁰ C and cooking times of from about 5 to about 45 minutes. Thus, neither extremely high temperatures nor longer heating times are required to produce the aroma according to the invention.

The aroma produced by the aroma precursor is grounded Poorly cooked or not cooked beef. This aroma can be modified by other additives, for example substituted thiazolidine carboxylic acids.

The flavor precursor can be added to numerous foods, which are advantageously meat-like

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Aroma should be given. The mixture is therefore used in food products such as real or synthetic Meat, starch-based foods or the like. A preferred application is use as a meat flavor precursor in meat substitute products from vegetable protein. Examples of such products include vegetable protein meat extenders, chopped or lump-like vegetable protein meat substitutes. The flavor precursor according to the invention can when used in combination with additional flavor and aroma components, the taste properties of food products, as described in US Pat. No. 3,399,015, to enhance. While the flavor precursor according to the invention a beef-like flavor similar to cooked beef is provided, additional flavor enhancers and to use flavor ingredients in combination therewith to enhance the taste and aroma of a food to deliver, change or strengthen. Aroma and flavor additives, for example flavoring agents, should be used in the form of amino acids, onion flavor, garlic, inorganic salts, pepper, sage, organic acids, Flavoring agents in the form of nucleotides and the like can be used in addition to the flavor precursor for the purpose Achieving a tasty, aromatic food with an authentic beef-juicy taste.

Furthermore, additional flavor modifiers can be used in combination be used with the flavor precursor according to the invention, For example, smaller amounts of lower saturated or unsaturated alkyl aldehydes such as acetaldehyde, butyraldehyde, valeraldehyde, Propanal and heptanal and the like. Lower alkyl ketones can also be used to change the aroma. These additional substances can be used in combination with the Product can be used as long as it is a

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have a positive effect on the taste or aroma of the end product. The above additional aroma modification agents are not essential, but are useful in producing certain desired authentic beef-like flavors.

It is not purely for the purposes of the present invention critical, however, to simulate certain beef products to prefer that one usually vegetable or animal fats or mixtures of these fats are added to the intermediate product in order to increase the fat content of the protein fiber. The fat content is adjusted to simulate a beef product. The type of fat is often after Elected for market reasons and the like. For example, one can use a vegetable fat like cottonseed oil, though unsaturated fat is desired in a meat substitute free of animal products. There is no aversion to the use of an animal fat, one can incorporate such fats into the fiber to obtain the desired To achieve the amount of fat. Other ingredients such as flavoring agents, color, σεί ^ ΐΓζ and the like can also be used added to the fat when simulating a beef product.

The following examples are intended to illustrate but not limit the present invention:

example 1

A mixture for a flavor precursor is prepared by first preparing a dimethyl sulfide precursor by adding 0.0468 g of S-methyl methionine to 52 g of mild, dry (4 % moisture) granular soy protein. Mix in 58 ml v / ater and allow the mixture to hydrate,

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then it is freeze-dried. About 1.4l parts of this granular freeze-dried dimethyl sulfide precursor material

T with 51.2 parts of mild soy protein, 23.0 parts of Fri-al (Mixture of animal / vegetable fat) and 0.18 parts of L-cysteine hydrochloride monohydrate mixed.

Cooking is done by boiling 145 ml of water and that Mixture mixed with it. The mixture is removed from the heat source, stirred, left to stand, covered, for 5 minutes and evaluated. Experienced odor testers describe the aroma above the liquid as beef-like.

Example 2

Evaluation of the aroma of an aroma precursor made from cysteine, SMM and proteins,

Three samples were made (See Table 1)

Table 1

T sample mild soy L-cysteine SMM sol. Fri-al water (ml)

protein (g) (g) (ml) fat (using wooden balls free base 1 mg / ml filtered)

45 6.0 0.12 - 2.6 16.5 86 6 _s 0 - 3.5 2.6 13.0 32 6.0 0.12 3.5 2.6 13.0

All ingredients were placed in a 235 ml vessel, mixed with a spatula, cover with lid and 10 minutes. ^ Then cooked another 10 min. Placed on a hot plate of 70 ⁰ C "was then evaluated the flavor of the samples from experts, see Table la.

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Table la

sample

Cysteine alone

SMM
alone

combination

Aroma intensity

(45)

X = 6.0

(86)

(32)

χ = 5.4 χ = 6.4

meaty inten- _
sity X = 3.0

χ = 3.4 χ = 4.4

Intensity of
Premd odor

X = 4.8

X = 3.8 X = 3.8

All samples were received within 45 minutes of their preparation rated. It should be noted that sample 32 makes the best impression made for overall meaty flavor and associated with sample 86 by equal values for premd taste was. A scale from 1 to 9 was used. X represents the mean of the intensity ratings. The experts found that sample 32 was a more intense meaty one Aroma possessed as samples that contained either cysteine or SMM alone.

Example 3

Evaluation of the influence of fat on the aroma of a precursor made from cysteine, SMM and protein. Three samples were made:

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Tabel

Sample of mild soy L-cysteine SMM solution. protein (g) (g) (ml)

free base 1 mg / ml fat

Water (ml) filtered through charcoal

39 6.0

0.12

3.5

13.0

27 6.0

0.12

3.5

Pri-al ¹ = 2.8 13.0

6.0

0.12

3.5 vegetable oil

= 2.8 13.0

. Found All ingredients were charged into a 235 ml vessel, mixed with a spatula, covered with lid and 5 min. Cooked, then 15 min on heating plates of 70 ⁰ C. The aroma of the samples was determined as in Example 2.

Table 2a

sample

39 (none)

27 _φ 61

(Fri-al- ¹ fat) (vegetable oil)

Aroma Intensity X = 5.4

X = 5,

X = 5.2

meaty intensity

X = 3.00

X = 4.6

X = 2.6

Intensity of foreign smell

X =

X = 4.0

X = 5.2

Fri-al is a deodorized mixture of animal and vegetable fat with about 90 % animal fat, including beef tallow,

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Al

It can be seen that the fat fri-al has the meat-like aroma of the pre-product mixture increased. All samples were evaluated within 45 minutes of their preparation.

Example 4

Deodorized and textured soy flakes were hydrated with water in the amounts shown in Table 3. Possibly the cysteine and / or SMM were added to the water. After hydration, the soy flakes became carefully mixed with ground beef, in loaves of each

3 g molded and held at 177 ° C for 3 minutes on each side fried, then the total meat character was assessed by trained examiners. Be under "Overall meat character" Understand the authentic meat structure, taste and aroma.

Ground beef
(G) Table 3 water Cysteine SMM sample 350 So j af lure " ¹ " 100 0.4 1 350 50 100 0.8 - 2 350 50 100 - 0.0125 3 350 50 100 - 0.0025 4th 350 50 100 0.4 0.0125 5 350 50 100 0.4 0.0075 6th 350 50 100 0.2 0.0075 7th 350 50 100 0.15 0.005 8th 50

+) deodorized, textured soy flakes that are modified by small amounts of flavorings.

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The examiners assessed the samples which contained the preliminary product mixture according to the invention (samples 5 to 8) against the other samples (1 to 4) for the overall meat character. It should be noted that all samples have the same composition, apart from the cysteine variable and SMM. It was also found that cysteine and SMM produced aroma at the levels used in Sample 8, but did not produce any taste when tasting with the nose closed »

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Claims (10)

Claims 1. Pre-product of a meat flavor, characterized by A. a hydrogen sulfide precursor; B. a? Dimethyl sulfide precursor and C. an edible proteinaceous material, the Hydrogen sulfide precursor, the dimethyl sulfide precursor and the proteinaceous material in quantities ,. the. , are _ ^ _n . ,,. are effective for producing a meat-like Aromas when the mixture of precursors is heated in an aqueous medium. 2. Pre-product according to claim 1, characterized in that A. The hydrogen sulfide precursor from cysteine, edible Salts of cysteine, glutathione, edible salts of glutathione or edible proteinaceous Sulfhydryl or cysteine; B. the dimethyl sulfide precursor from edible salts or Derivatives of S-methyl-methionine, S-methyl-4-methylthiobutyric acid, S-methyl-methylcysteine, S-methyl-3-methylthiopropionic acid or S-methyl-methylthioacetic acid consists. 3. Pre-product according to claim 2, characterized in that they an edible thiazolidine in the form of a thiazolidine reducing sugar :, aldehyde thiazolidine or ketone thiazolidine which is a stable precursor of cysteine. ORIGINAL INSPECTED 030010/0591 4. Pre-product according to claim 1, characterized in that it is soy protein as the proteinaceous material contains. 5. Pre-product according to claim 1, characterized in that it is cysteine and hydrogen sulfide precursor contains S-methyl-methionine as dimethyl sulfide precursor, wherein the effective amount of the cysteine is from about 100 to about 50,000 ppm part © of the protein food and the amount of S-methyl-methionine from about 0.25 to about 700 ppm TeIF of the proteinaceous food. 6. Pre-product according to claim 5 * characterized in that that the amount of cysteine is about 1,000 to about 15,000 ppm and the amount of S-methyl methionine is about 25 to about 175 ppm. 7. Pre-product according to claim 5 *, characterized in that the amount of cysteine is about 2,000 to about 5,000 ppm. 8. A method for producing a meat-like flavor in edible protein-containing materials, characterized in that that one aroma precursor in an aqueous medium at a temperature of about 60 to about 180 ° C Boils for about 5 to about 45 minutes, with the precursor consists A. a hydrogen sulfide precursor; B. a dirnethyl sulfide precursor and C. an edible proteinaceous material, the hydrogen sulfide precursor being the dimethyl sulfide precursor and the proteinaceous material in quantities are present that are sufficient to achieve a meat-like flavor when heating the pre-product mixture in watery environment. 030010/0591 9. The method according to claim 8, characterized in that that the precursor of hydrogen sulphide is cysteine, edible salts of cysteine, glutathione, edible salts of glutathione, or edible protein-containing sulfhydryls or cystine and edible as dimethyl sulfide precursor Salts or derivatives of S-methyl-methionine, S-methyl-4-methylthiobutyric acid, S-methyl-methylcysteine, S-methylj5-methylthiopropionic acid or S-methyl-methylthioacetic acid is used. 10. The method according to claim 9 *, characterized in that cysteine is used as the hydrogen sulfide precursor and S-methyl-methionine as the dimethyl sulfide precursor, the effective amount of cysteine being about 100 to about 50,000 ppm -Methyl methionine is about 0.25 to about 700 ppm parts of the proteinaceous material .. 030010/0591